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Top 15 Most Awkward On-Screen Celebrity Kisses

What makes a kiss awkward? What makes anything awkward? In this day-and-age, "awkward" is the kiss of death, in Hollywoodland especially, where smooth social interaction is real currency; and in a place where people pretend to get along both on-screen and off, and where at any turn you might realize you are in a reality TV series or on a prank show, and have a release shoved in your face alongside false promises of a break into the acting world, there are all manner of opportunity for the weirdness of forced smiles and affection to bleed through the camera lens.

Some of the following images have a real-world backstory that make the fact that two particular actors were forced to lock lips ironic, other scenes are physically strange, between two characters that are genuinely or for comedic effect weird and uncomfortable to watch, and still other shots are of two actors playing characters that typically are not accepted as romantically compatible by the superficial social policy of the film world; big age differences, incestuous kisses, scenes that tweens and teens are too emotionally undeveloped to the handle, these also, or perhaps especially, fall under the umbrella of "awkward."

High school and Hollywood are actually strikingly similar environments, the things that are labeled strange and out-there do not necessarily get swept under the rug, instead they get run up the flagpole for all to see; but pranksters like Matt Stone and Trey Parker still get their kisses on screen to make the jocks and conservative parents cringe, teenagers still get their kisses that have long been awaited between Twilight or Harry Potter characters they've been following since the beginning that they can laugh at as they secretly take notes to avoid the same awkwardness in their own pubescent fumbling, and the gossip swirling around offscreen Hollywood romances and torrid affairs adds extra drama to fake onscreen kisses, just like rumors of teen pregnancy made the prom king and queen holding hands that much more salacious. So, without further rambling and ado, enjoy the following list of fifteen variously quote-unquote "awkward," uncomfortable, squirm-inducing shots of mostly well-known actors and actresses locked in weird lip action.

15 Kim Basinger and Dana Carvey in Wayne's World

via: youtube.com

This is one of those onscreen kisses that was meant to appear incredibly awkward for comedic effect; throughout the Wayne's World series of films, SNL alum Dana Carvey's nerdy wannabe rocker, Garth Algar, demonstrates some serious(ly funny) quirks and neuroses, among them an inability to interact smoothly with sexy exemplars of the opposite sex. Still, it is easy to imagine the Montana-born stand-up comedian turned movie star did not have to do much acting to portray a jittery non-entity next to Kim Basinger's striking and angular beauty, not to mention her pedigree as a serious actor up until her cameo in this awkward on screen romance. That is to say, neither Carvey nor Basinger probably had to put up much of a facade to appear respectively hopelessly awkward and self-assuredly sexy.

14 Joe Pesci and Sharon Stone in Casino

via: youtube.com

What makes this kiss most awkward is not the fact that Joe Pesci is a New Jersey boardwalk troll even next to Sharon Stone's desperate and out-of-control (but still enticing) character in 1995's gangster drama, Casino, nor the fact that the two actors cannot seem to lock onto each other's lips, but what makes this kiss the most "awkward" is the fact that it devolves into fellatio about ten seconds in. Pesci's character, Nicky Santoro, is, like most of the characters this Italian-American actor portrays, a self-interested and volatile (i.e., violent and unpredictable) thug who, in this scene, has essentially taken advantage of his best friend's wife's emotional state to the tune of some insensitive heavy petting.

13 Paul Rudd and Elizabeth Banks in Wet Hot American Summer

via: youtube.com

Before it was a Netflix original series, Wet Hot American Summer was an independent movie with a small but devoted cult following. The specific people for whom this 2001 film hit home were nostalgic summer-camp kids, campers and counselors alike, and the same folk that fell in love with what could be labeled retro period pieces like Judd Apatow's Freaks & Geeks. The Netflix spinoff series is unique in that it stars many of the original cast members of the film that spawned it, including Paul Rudd and alternative comedy godmother, Janeane Garofalo. The screencap pictured here says it all about this awkward onscreen kiss, but feel free to check out this soon-to-be runaway cult classic, again.

12 Ape Shall Never Kiss Ape, The Reboot

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If only the major tenet of the law-abiding apes' code from the original (1968) Planet of the Apes were, "Ape Shall Never Kiss Ape," rather than the actual, "Ape Shall Never Kill Ape," then maybe kisses like the one pictured here would be more commonplace in the Planet of the Apes franchise universe, but then again, less conflict between man and ape means fewer tickets sold. The kiss pictured here, between Matt Damon and what or who I believe is Helena Bonham Carter, Tim Burton's wife of thirteen years (divorced in 2014 for inquiring minds), under wig, heavy makeup, and latex face alterations, playing lady ape/humanoid, Ari. This list item could just as easily have been a shot from the original film that featured an equally awkward trans-species kiss between Charlton Heston and a female human-turned-ape.

11 Kirsten Dunst and Tobey Maguire in Spider-Man

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Kirsten Dunst was twenty years old and squarely in the category of people called "women" by the time she appeared on screen kissing Tobey Maguire in 2002's Spider-Man, so unlike her lip locking with Brad Pitt on the set of Interview With The Vampire (see list item number 3 below), this time the awkwardness stemmed from the actual staging of the kiss in question, the purely physical difficulties of kissing somebody who is hanging upside down in the rain, wearing what is essentially a ski-mask. Maguire himself has told the tabloid press that it is practically impossible to breath with a superhero mask covering one's nose and a cute co-star's face covering one's mouth, and all the while water dripping up one's face.

10 Brangelina in Mr. And Mrs. Smith

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None of the on screen passion shared between Brad Pitt and Angelina Jolie in this film is necessarily awkward as it appears on screen, but knowing what was occurring in the movie stars' romantic lives off screen at the time this film was released makes the scripted romance ironic at best, and impossible to believe at worst. Mr. And Mrs. Smith was released in 2007, two years after Brangelina formed to the demise of Brad Pitt and Jennifer Aniston's marriage. In the movie, the lovers exchange as many bullets as they do kisses, and express just as much hate as they do love; in an analogous way, Brangelina's union off the studio backlot was just as anticipated as begrudged by nosey fans and paparazzi worldwide.

I guess we should have seen the divorce coming.

9 Hermione Grows Up in Perks of Being a Wallflower

via: youtube.c

This movie is about awkwardness, plain and simple--more specifically The Perks Of Being A Wallflower, is about those crazy, messy first relationships that are bound to be painfully awkward, replete with fumbly/grope-y face sucking explorations, jealousy-laden love triangles, and hearts breaking and mending on a dime. Hence, the scene pictured here is definitely not the only scene in the movie that features young actors pretending, to some presumably small degree, to be their awkward young adult selves. This scene is just the most obviously uncomfortable in the film, and instead of sweet nothings, the scene features a voiceover from leading lad Logan Lerman, complaining about being bored with the breasts he otherwise seems to be enjoying in this shot.

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8 Lauren Holly and Jim Carrey in Dumb & Dumber

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Obviously, this kiss is meant to be funny, but knowing the actor literally sucking Lauren Holly's face in this scene was romantically involved with the redheaded beauty off screen at the time comedy classic/milestone Dumb & Dumber was released, makes the slapstick humor and literal physical awkwardness somewhat ironic in comparison to what was presumably much less awkward (if still equally steamy private) romantic encounters. Before proving himself as a dramatic actor first in The Truman Show, Jim Carrey was known for his physicality and slapstick sensibilities both as a stand-up comedian and as a mainstay on alternative sketch comedy show In Living Color. The kiss pictured here hearkens back to Carrey's sillier days.

7 An Incestuous Kiss in Eurotrip

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This kiss is purely quote-unquote "awkward" for the relationship between the two characters sucking each others faces in this screencap from 2004's flick, EuroTrip; long story short: the two characters (not-so-memorably played by post-teen flavor of the month heartthrob Michelle Trachtenberg and still active but still unknown young adult hotty Scott Mechlowicz) are siblings and are too inebriated and/or caught up in the heat of the moment to realize they are kissing each other (i.e., blood relatives). Of course EuroTrip was written as a comedy, so this kiss also is slapstick funny in a calculated way, the timing and movement of this hot and heavy moment is meant to be as uncomfortable as brother and sister's realization they have crossed that taboo line.

6 Woody Allen, Helen Hunt, Curse Of The Jade(d) Scorpion

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There is something hilarious but also slightly creepy going on when an Academy Award-winning filmmaker like Woody Allen, on multiple occasions, writes himself parts opposite actresses who make him look even more lecherous and old than he appears or comes across in the gossip rags or in publicly-available court records. That's right, this is not the only scene or even movie that features a scene where bumbling, neurotic Allen wrote himself into the arms of someone otherwise way out of his league, it is just one of the more painfully mismatched romantic moments in the Ashkenazi comedic actor's catalog of classic movies. Convoluted musings aside, Woody Allen no longer has any business playing romantic interests in his own movies, at least opposite attractive female leads.

5 Will Ferrell Vs. Leslie Bibb in Talladega Nights

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Talladega Nights and The Ballad of Ricky Bobby heat up in this scene that shows the moral decline of the Bobby family and entourage (a.k.a. John C. Reilly's Cal Naughton, Jr.) in the face of fame and fortune. Ricky and Carley Bobby's children, disgruntled in-law, and underappreciated best friend and teammate racer, all look on as they go to town on each other like horny teenagers, half wrestling, half dry humping each other to the dinner table in a jumble of limbs that make it actually very hard to discern whether Will Ferrell and sexy, sassy blonde actress Leslie Bibb, are engaged in an act of aggression or romance, squarely landing this moment in the category of awkward on screen celebrity kisses.

4 Man (Rudd) Loving Man (Lennon) in I Love You, Man

via: youtube.com

Just right off the bat, this kiss is not awkward solely because it is between two men; that would be homophobic to feel uncomfortable simply for the fact that two men are romantically engaged on the big screen. What makes this kiss quote-unquote "awkward" in the context of the plot of this hilarious buddy comedy flick often falsely attributed to the Judd Apatow machine, is the fact that only one of the men in this frame is homosexually inclined; signals have been misread in this sequence and it is the explanation for the cigarette taste in Rudd's, playing already-incredibly socially awkward real estate agent Peter Klaven, mouth when later in the film kissing fiancee Zooey Rice, played aptly by Rashida Jones.

3 Kirsten Dunst and Brad Pitt in Interview With The Vampire

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In interviews about her on screen romance with heartthrob Brad Pitt in 1994's Interview With The Vampire: The Vampire Chronicle, now a fully grown woman, Kirsten Dunst has to remind audiences and fans that she was only eleven years old at the time this film broke her into the mainstream; most 11-year-olds (at least back in the 1990s) were pre-pubescent and therefore Brad Pitt, sexy to most living females at the time, still essentially had "cooties" in the eyes and mind of young Kirsten. Still, her young age and asexuality most likely did not stop fans of the now-proven actress from falling equally in love with Dunst's acting chops as with her babydoll looks back then.

2 The Creators Of BASEketball Get Hot 'n' Heavy On Set

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Another kiss meant to be over-the-top and hard to watch but in a comedic way, but unlike the man-on-man love expressed by Paul Rudd and Thom Lennon in I Love You, Man, the comedy in this slice of 1998's absurdist comedy BASEketball stems both from the physical or slapstick element (i.e., the fact that two protagonists are more interested in making tongue-contact than "kissing" per se) and the fact that the two protagonists' sexuality has not been made explicit up until this point in the movie, nor are the two actors, Matt Stone and Trey Parker, known better for South Park and The Book Of Mormon, outspoken about their sexuality off screen or outside of the voiceover booth, so this kiss flies in the face of the audience's heteronormative expectations.

1 Kristen Stewart and Jesse Eisenberg in Café Society

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Jesse Eisenberg epitomises the term "awkward", and that alone earned this on screen romance the top spot on this list. Cafe Society was released in theaters on August 5th, to a much more muted fanfare than Woody Allen movies used to fetch back in the 70s-through-the-00s. Perhaps it is the recent legal flare up of decades old habits of sexual impropriety in the news this year (2016) or maybe Scarlett Johansson Yoko Ono'd Woody Allen's credibility as a legitimate filmmaker or as somebody who still has something novel and fresh to contribute to the art form. Marc Maron and Billy Crystal joked on a recent episode of the WTF Podcast that of the things Crystal awaited in childhood was included the new Woody Allen movie; perhaps his legacy is getting stale and his fans are getting tired of looking the other way on the movie maker's own torrid off-screen exploits while he continues to corner the market on the awkward romantic comedy.